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HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases

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Abstract

The separation of enantiomers of 14 chiral carboxylic acid derivatives was studied on six different polysaccharide-based chiral columns in high-performance liquid chromatography with methanol, ethanol and acetonitrile as mobile phases with emphasis on the elution order of enantiomers. Some interesting examples of enantiomer elution order reversal were observed as a function of the nature and composition of chiral selector and mobile phase. For instance, the enantiomer elution order for carprofen, ketorolac, naproxen, proglumide and surprofen reversed with changing the chemical structure of the chiral selector. Also, the enantiomer elution order for carprofen, ketorolac and naproxen changed by varying the composition of the mobile phase. In addition, the interesting effect of column temperature on the retention and separation of some analytes was observed. For instance, the enantiomers of surprofen were only partially resolved at lower temperatures but baseline resolved at higher temperature.

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Abbreviations

EEO:

Enantiomer elution order

CSP:

Chiral stationary phase

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The authors declare no conflict of interests.

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Authors and Affiliations

  1. Institute of Physical and Analytical Chemistry, School of Exact and Natural Sciences, Tbilisi State University, Chavchavadze Ave 3, 0179, Tbilisi, Georgia

    Iza Matarashvili, Lali Chankvetadze & Bezhan Chankvetadze

  2. Department of Pharmaceutical Chemistry, Faculty of Chemistry, Georgian Technical University, Kostava Str. 77, 0102, Tbilisi, Georgia

    Tamar Tsintsadze

  3. Phenomenex Inc, 411 Madrid Ave, Torrance, CA, 90501, USA

    Tivadar Farkas

Authors
  1. Iza Matarashvili
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  2. Lali Chankvetadze
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  3. Tamar Tsintsadze
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  4. Tivadar Farkas
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  5. Bezhan Chankvetadze
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Correspondence to Bezhan Chankvetadze.

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Matarashvili, I., Chankvetadze, L., Tsintsadze, T. et al. HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases. Chromatographia 78, 473–479 (2015). https://doi.org/10.1007/s10337-015-2852-8

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  • DOI: https://doi.org/10.1007/s10337-015-2852-8

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